Coating composition having accelerated drying time and the process of accelerating same



Patented Nov. 3, 1 953 old-HEB stares PATENT (TFFICE.

en gma; composition HAVING? AGGELER-F aicpo nlyy gc rnus THE: moons-s 0F ACCELERATING SAME Ntfimwiiig app ication June 23, 1951, sonar No. 233,252

16 0mm. (o1. mc zt n This invention relates to new coating: compositions comprising a drying vehicle: and. an improved drier therefor; More: particular-1y the" siccative are polyvalent drier metalsalts of morioalkylesters of diisobutenylsu'ccihic acid and triisobu-teny-l's'un'cinic' acid, wherein the alkyl group contains from: to 4 carbon atoms, inelusive: More? particular-1y still the drier metal is selected from the preferred group' of poly va'lent metals. consisting. of lead, cobalt; mang'anese; and zinc.

The prior artdri'er' sare resinates, linoleates and naphtlienates of the polyvalent driermetals. The resinate and linoleatetype" driers oxidize very readily. becoming insoluble in the coating solvents and: the drying vehicle,- thus they must be u'sed within a" relatively short time after they are made-. Also these: driers' may spontaneously ignite in storage and are accordingly a definite fire hazard. The naphthenates in general have improved solu-bilities' and: greater stability than the resinates and linol-eates; but have: an odor which is disagreeable to many consumers; In addition, the naphthenic acids are currently in short supply, pointing: up the necessity of finding other suitable drier com-positions;

One object of the presentinvention is to provide coating compositions which are characterized by faster drying properties Another object of the present invention is to provide an improved drier which possesses goodsolubility in organic solvents employed;- in the coatings in dustry and in the drying: vehicle; A further ob jec-t that the driers a-re substantially free of objectionable odors Yet another object is to provide driers which are stable when exposed tooxid ation conditions.

It has now been found that: the polyvalent drier metal salts of monoalkyl esters of diisobutenylsucoinic acidand triisobutenylsuccinic acid with drying vehicles provides an improved coating composition which has faster drying properties than with conventional commercial driers; and the drier is characterized by good solubilityin coating solvents and drying v'e* hicles; is exceptionally stable against oxidation, notwithstanding the presence of. the alkenyl group; is substantially free of an'y disagreeable odor; and is capable of volume production from available-raw materials;

v the" term "pmyvarehtdri'e'r near" it is uhderst'obd the eaivehubhai dii'ers" meant;

prerhed dri'er metals are lead, cobalt; man-ganeses and zinc, not other metals; such alliiniiiufii', calcium, cerium, chromium: copper;

iron; nickel, and vanadium may also be employed. The latter metals are not as active as" theformefgroupg but a-re oite'n beneficially eh:- ploye'd therewith for special" eliects andare accordingly within the scope or this" invention: Thus, mixed driersi area-13dunderstood to be within the scope of this invention.

In general the conv'eri'tiona1v quantities of the dii'e'rs', reported as Weight per cent or" metal" based" the W'eigh't' (if the dry ng vehicle solids.

are employeu. preferablyffoni atone-.21 to about 0.5 per cent of lead is generallyusd, although up to 2.0 pendent and eveiihig hei-"ma y' be incorhorated for: special: effects; The surface drying metals, cobalt and manganese) are-normaiiy used: within a= range of from about 9301 to about 0.1 per cent, but here too higher quantitiesam'ay be eimiloyed for specific results a stfor' example, the production of a wrinkle The term drying vehicle? iserriployd herein to mean a fluid organic composition which sets oxidationand polymerization, as rorexam ple"; drying oil's, paints, lacquers; enamels, nishes, styrenated alkyds and similar resinous coating materials:

The onersare prepared for use by dissolving in a conventional solvent, as for example; min eral spirits, V. M. and P. naphtha, xylene tolu ene and benzene. Ccincentrat'ed solutions containing more than 50 per cent solidscan be pre-- pared} as for example,- cobalt monomethyl diisobutenylsuccinatein mineralspirits." I

The followingexamples areillustrative oi the invention:

. Eaiamplcl A loiig' nsee'doilm'odifi'edplithalic anlfi'ydfi'de pentaerythr'itol alkyd r'es'iii having a viscosity of i; at 7o per cent' solids in mineral spirits was further out to about-to per cent solids with additional" mineral spirits. 'ro two samples or the aforesaid resin 0102 Weight per cent o'frhetal based the; weight r the alkyd" resinsolids are; cobalt drier was" added; sample A contained cobalt" naphthenate' airdf sample 13 contained cobalt monometliyl diisobutenylsuccinate; The" samples were aged briefly and then applied as a 0.002 inch film on tin. Sample B comprising the composition of this invention was set in less than three hours whereas sample A was not set for a substantially greater period of time. It was particularly noted that the drier of sample B had no odor as compared to the cobalt naphthenate drier.

Example 2 A sample of bodied linseed oil was cut to about 70 per cent solids with mineral spirits. To each s Example 3 A long soybean oil modified phthalic anhydridepentaerythritol alkyd resin was cut to about 50 per cent solids by the addition of mineral spirits. To two samples of the above cobalt naphthenate (A) and cobalt monomethyl diisobutenylsuccinate (B) were added, respectively, such that 0.05 per cent of the cobalt drier based on resin solids was employed. Sample B was set in about 2 hours, dust-free in less than about 3 hours, and tack-free in less than about hours; whereas, sample A required, respectively, about 3 hours, less than 4 hours, and was not yet tackfree after about 5 hours.

Example 4 To five samples of castor oil modified phthalic anhydride-glycerol alkyd resin, out to 38 per cent solids with mineral spirits, 0.04 per cent of a cobalt drier based on resin solids was added as follows:

Sample A--Cobalt naphthenate Sample B-Cobalt monomethyl diisobutenylsuccinate Sample CCobalt monoisopropyl diisobutenylsuccinate Sample D-Cobalt monobutyl triisobutenylsuccinate Sample E--Cobalt octoate Sample B was found to set and become dust-free faster than the other samples, sample D was slightly faster than A and E, and sample C required a slightly greater time than A and E.

Other driers which can be employed are for example:

Lead monoethyl diisobutenylsuccinate Zinc monopropyl diisobutenylsuccinate Manganese monoisobutyl diisobutenylsuccinate Lead monomethyl triisobutenylsuccinate Zinc monoethyl triisobutenylsuccinate Manganese monopropyl triisobutenylsuccinate The drier metal salts, for example, cobalt, manganese, and lead salts of diisobutenylsuccinic and triisobutenylsuccinic acids were found to be useless as driers in that they were insoluble in coating solvents and accordingly failed to meet one of the major requirements of a drier. The monoalkyl esters of the aforesaid acids containing more than four carbon atoms also have poor solubility and the progressively smaller weight ratio of the drier metal to the molecular weight of the compounds also is detrimental.

We claim:

1. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of a drier comprising a polyvalent drier metal salt of the monoalkyl esters of diisobutenylsuccinic acid and triisobutenylsuccinic acid, wherein the alkyl group contains from 1 to 4 carbon atoms, inclusive.

2. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of a drier comprising a drier metal salt of the monoalkyl esters of diisobutenylsuccinic acid, wherein the drier metal is selected from the group consisting of lead, cobalt, manganese, and zinc and mixtures thereof, and the alkyl group contains from 1 to 4 carbon atoms, inclusive.

3. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of a drier comprising a drier metal salt of the monoalkyl esters of triisobutenylsuccinic acid, wherein the drier metal is selected from the group consisting of lead, cobalt, manganese, and zinc and mixtures thereof, and the alkyl group contains from 1 to 4 carbon atoms, inclusive.

4. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monomethyl diisobutenylsuccinate.

5. A coating composition comprising a drying vehicle and an efiective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monoisopropyl diisobutenylsuccinate.

6. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monobutyl triisobutenylsuccinate.

'7. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of lead monomethyl diisobutenylsuccinate,

8. A coating composition comprising a drying vehicle and an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of manganese monomethyl diisobutenylsuccinate.

9. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of a polyvalent drier metal salt of the monoalkyl esters of diisobutenylsuccinic acid and triisobutenylsuccinic acid, wherein the alkyl group contains from 1 to 4 carbon atoms, inclusive.

10. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an efiective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of a drier metal salt of the monoalkyl esters of diisobutenylsuccinic acid, wherein the drier metal is selected from the group consisting of lead, cobalt, manganese, and zinc and mixtures thereof, and the allryl group contains from 1 to 4 carbon atoms, inclusive.

11. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying .vehicle solids, of a drier metal -salt of the monoalkyl esters of triisobutenylsuccinic acid, wherein the drier metal is selected from the group consisting of lead, cobalt, manganese, and zinc and mixtures thereof, and the alkyl group contains from 1 to 4 carbon atoms, inclusive.

12. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monomethyl diisobutenylsuccinate.

13. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an effective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monoisopropyl diisobutenylsuccinate.

14. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an effective amount up to about 2 6 per cent by weight of metal, based on the weight of the drying vehicle solids, of cobalt monobutyl triisobutenylsuccinate.

15. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an efiective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of lead monomethyl diisobutenylsuccinate.

16. The process of accelerating the set of a drying vehicle, which comprises mixing with the drying vehicle an efiective amount up to about 2 per cent by weight of metal, based on the weight of the drying vehicle solids, of manganese monomethyl diisobutenylsuccinate.

LQUIS E. KLIEN. AUGUST R. HEMPEL.

References Cited in the file of this patent UNITED STATES PATENTS Number 

1. A COATING COMPOSITION COMPRISING A DRYING VEHICLE AND AN EFFECTIVE AMOUNT UP TO ABOUT 2 PER CENT BY WEIGHT OF METAL, BASED ON THE WEIGHT OF THE DRYING VEHICLE SOLIDS, OF A DRIER COMPRISING A POLYVALENT DRIER METAL SALT OF THE MONOALKYL ESTERS OF DIISOBUTENYLSUCCINIC ACID AND TRIISOBUTENYLSUCCINIC ACID, WHEREIN THE ALKYL GROUP CONTAINS FROM 1 TO 4 CARBON ATOMS, INCLUSIVE. 